Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | o-Toluenesulfonyl chloride | HCID 8623 | — |
| Reactant | HCID 24808701 | HCID 24808701 | — |
| Catalyst | Dibutyltin oxide | HCID 61221 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 57385996 | HCID 57385996 | 80.4% |
Reaction Steps
Diol (1) (1.560 g, 13.667 mmol) was dissolved in DCM (140 mL) cooled to 0° C. and dibutyltin oxide (67.9 mg, 0.2728 mmol), triethylamine (2.08 mL, 1.518 g, 15.005 mmol) and toluenesulfonyl chloride (2.864 g, 15.022 mmol) were added. After 10 minutes the icebath was removed and the reaction mixture was stirred for 22 hours. Then it was filtrated and the filtrate concentrated in vacuo. Purification by chromatography (hexane/EtOAc 4/1) provided 2.950 g of compound (2a) as clear colourless oil with 80% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08809395B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-85d91a524c6a472f81469e2938a7134c |
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| Source note | uspto-grants-2014_08 |
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